Facile and convenient synthesis of aryl hydrazines via copper-catalyzed C–N cross-coupling of aryl halides and hydrazine hydrate

Kurandina, Daria; Eliseenkov, E. V.; Ilyin, Petr V.; Boyarskiy, Vadim P.

doi:10.1016/j.tet.2014.04.048

Cited by 21 publications

(7 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…11 However, the synthetic utility of these methods are greatly restricted because of the limited availability of arylhydrazines due to their inherent instability issues and difficulties in their synthesis. 12 Therefore, the development of an alternative method for the synthesis of arylhydrazones from readily available starting material is essential. 13 Based on our hypothesis, nitrosobenzene was reacted with benzylamine in the presence of 2,4-dichlorobenzoic acid (DCBA), which is used to facilitate dehydration ( Table 1, entry 1).…”

Section: Scheme 1 Reaction Of Amines With Nitrosoarenesmentioning

confidence: 99%

N-Aminations of Benzylamines and Alicyclic Amines with Nitrosoarenes to Hydrazones and Hydrazides

Purkait¹,

Jana

2019

Synthesis

View full text Add to dashboard Cite

Unlike other alkylamines, benzylamines upon reaction with a nitrosoarene undergo oxidation to the corresponding imines. A direct amination of benzylamines, which was difficult to achieve due to its facile oxidation, to the corresponding hydrazones is reported. A wide variety of benzylamines and N-heterocycles were reacted with nitrosoarenes to provide structurally diverse hydrazones and hydrazides, respectively. Moreover, the direct N-amination reaction was applied to the one-pot synthesis of triazoles.

show abstract

Section: Scheme 1 Reaction Of Amines With Nitrosoarenesmentioning

confidence: 99%

N-Aminations of Benzylamines and Alicyclic Amines with Nitrosoarenes to Hydrazones and Hydrazides

Purkait¹,

Jana

2019

Synthesis

View full text Add to dashboard Cite

show abstract

“…Milder reactions occurred by forming oxalohydrazide ligands from the parent, unsubstituted oxalylhydrazide and a series of ketones, including 1,4‐diketones [19b] . The catalyst generated from isolated oxalohydrazide ligand L1 , formed from the 1,4‐diketone hexane‐2,5‐dione and oxalylhydrazide was reported to couple hydrazine with aryl bromides in water [19d] . We were unable to reproduce this coupling of hydrazine in water, most likely due to complications from the lack of solubility of the bromoarene and the oxalohydrazide ligand in this medium.…”

Section: Resultsmentioning

confidence: 99%

Oxalohydrazide Ligands for Copper‐Catalyzed C−O Coupling Reactions with High Turnover Numbers

Ray

Hartwig

2021

Angew Chem Int Ed

View full text Add to dashboard Cite

Here,w er eport ac lass of ligands based on oxalohydrazide cores and N-amino pyrrole and N-amino indole units that generates long-lived copper catalysts for couplings that form the CÀObonds in biaryl ethers.These Cucatalyzedc oupling of phenols with aryl bromides occurred with turnovers up to 8000, avalue which is nearly two orders of magnitude higher than those of prior couplings to form biaryl ethers and nearly an order of magnitude higher than those of any prior copper-catalyzed coupling of aryl bromides and chlorides.T his ligand also led to copper systems that catalyze the coupling of aryl chlorides with phenols and the coupling of aryl bromides and iodides with primary benzylic and aliphatic alcohols.Awide variety of functional groups including nitriles, halides,e thers,k etones,a mines,e sters,a mides,v inylarenes, alcohols and boronic acid esters were tolerated, and reactions occurred with aryl bromides in pharmaceutically related structures.

show abstract

“…Starting fluoronitroalkenes XC 6 H 4 CH=C(F)NO 2 ( 1a (X = p ‐Cl), 1b (X = p ‐F), 1c (X = p ‐CO 2 Me), 1d (X = p ‐OMe), 1e (X = p ‐Br), 1f (X = p‐ CF 3 ), 1g (X = o ‐Cl)) were prepared by radical nitration of corresponding fluorobromostyrenes by Fe(NO 3 ) 3 . [16e] Hydrazines were either purchased or prepared according to literature methods . TLC were performed on silica coated on aluminium with UV254 indicator.…”

Section: Methodsmentioning

confidence: 99%

Acid‐Mediated Three Component Assembly of 4‐Fluoropyrazoles from α‐Fluoronitroalkenes, Hydrazines, and Aldehydes

et al. 2020

View full text Add to dashboard Cite

A new approach for the synthesis of highly pharmaceutically relevant 4‐fluoropyrazoles via oxidative annulation of α‐fluoronitroalkenes with in situ prepared hydrazones was developed. The reaction is efficiently promoted by trifluoroacetic acid while atmospheric oxygen was used as an oxidant. Broad substrate scope was demonstrated, using both electron‐rich and electron‐deficient nitroalkenes as well as different hydrazones derived from aromatic aldehydes. The mechanistic details were also outlined.

show abstract

Facile and convenient synthesis of aryl hydrazines via copper-catalyzed C–N cross-coupling of aryl halides and hydrazine hydrate

Cited by 21 publications

References 23 publications

N-Aminations of Benzylamines and Alicyclic Amines with Nitrosoarenes to Hydrazones and Hydrazides

N-Aminations of Benzylamines and Alicyclic Amines with Nitrosoarenes to Hydrazones and Hydrazides

Oxalohydrazide Ligands for Copper‐Catalyzed C−O Coupling Reactions with High Turnover Numbers

Acid‐Mediated Three Component Assembly of 4‐Fluoropyrazoles from α‐Fluoronitroalkenes, Hydrazines, and Aldehydes

Contact Info

Product

Resources

About